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Substance Name: Melphalan flufenamide [INN]
RN: 380449-51-4
UNII: F70C5K4786
InChIKey: YQZNKYXGZSVEHI-VXKWHMMOSA-N

Note

  • NCI: A melphalan prodrug in which the alkylating agent melphalan is bound to flufenamide, with potential antineoplastic and anti-angiogenic activities. Upon administration, the dipeptide bond in the melphalan-flufenamide compound is hydrolyzed by peptidases, which are overexpressed by certain cancer cells. This results in the specific release and accumulation of the active metabolite melphalan in cancer cells. Melphalan alkylates DNA at the N7 position of guanine residues and induces DNA intra- and inter-strand cross-linkages. This results in the inhibition of DNA and RNA synthesis and the induction of apoptosis, thereby inhibiting tumor cell proliferation. The administration of the melphalan-flufenamide prodrug allows for enhanced efficacy and reduced toxicity compared to melphalan alone. (NCI Thesaurus)

Molecular Weight

  • 498.423
 
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Names and Synonyms

Name of Substance

  • Melflufen
  • Melphalan flufenamide [INN]

Synonyms

  • Ethyl (2S)-2-((2S)-2-amino-3-(4-(bis(2-chloroethyl)amino)phenyl)propanamido)-3-(4-fluorophenyl)propanoate
  • J 1
  • J 1 (prodrug)
  • J-1
  • J-1 (prodrug)
  • L-Phenylalanine, 4-(bis(2-chloroethyl)amino)-l-phenylalanyl-4-fluoro-, ethyl ester
  • Melphalan flufenamide
  • MFF
  • Prodrug J 1
  • Prodrug J-1
  • UNII-F70C5K4786

Registry Numbers

CAS Registry Number

  • 380449-51-4

FDA UNII

  • F70C5K4786

System Generated Number

  • 0380449514

Structure Descriptors

InChI

1S/C24H30Cl2FN3O3/c1-2-33-24(32)22(16-18-3-7-19(27)8-4-18)29-23(31)21(28)15-17-5-9-20(10-6-17)30(13-11-25)14-12-26/h3-10,21-22H,2,11-16,28H2,1H3,(H,29,31)/t21-,22-/m0/s1

InChIKey

YQZNKYXGZSVEHI-VXKWHMMOSA-N

Smiles

CCOC(=O)[C@H](Cc1ccc(F)cc1)NC(=O)[C@@H](N)Cc2ccc(cc2)N(CCCl)CCCl